Copper-Catalyzed Arylation and Subsequent Cyclization of Terminally Functionalized Propargyl Silanes

83rd International Scientific Conference of the University of Latvija 2025. Chemistry Section and Section of Institute of Chemical Physics: Book of Abstracts 2025
Rasma Kroņkalne, Rūdolfs Beļaunieks, Armands Sebris, Māris Turks

Recently we have published synthesis methods for propargyl silane 1,3-difunctionalization with concomitant silyl shift [1]. The concept involves propargyl silane activation with an electrophile, followed by a 1,2-silyl shift. This creates an electrophilic carbon center that can react with a nucleophile. This work presents the use of hypervalent iodine(III) reagents as formal carbon electrophiles to activate the propargyl silane moiety. The reaction proceeds via formation of the aryl cuprate from diaryliodane, which activates the propargyl silane to undergo the 1,2-silyl shift. T his generates a carbenium ion or its equivalent, which is trapped by the internal nucleophile (alcohol or amide) present. A variety of aromatic groups with electron donating and electron withdrawing substituents was successfully applied in this reaction, as well as some heteroaromatic groups.

Keywords
Copper catalysis; iodanes; propargyl silanes
DOI
10.22364/iscul.83.cs.ba
Hyperlink
https://www.apgads.lu.lv/fileadmin/user_upload/lu_portal/apgads/PDF/Konferences/2025/iscul-83-cs-ba.pdf

Kroņkalne, R., Beļaunieks, R., Sebris, A., Turks, M. Copper-Catalyzed Arylation and Subsequent Cyclization of Terminally Functionalized Propargyl Silanes. In: 83rd International Scientific Conference of the University of Latvija 2025. Chemistry Section and Section of Institute of Chemical Physics: Book of Abstracts, Latvia, Rīga, 14-14 February, 2025. Riga: University of Latvia, 2025, pp.40-40. ISBN 978-9934-36-369-6. Available from: doi:10.22364/iscul.83.cs.ba

Publication language
English (en)